New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties

被引：31

作者：

Duarte, Rodrigo da Costa ^{[1
]}

Ongaratto, Renata ^{[1
]}

Piovesan, Luciana Almeida ^{[1
]}

de Lima, Vania Rodrigues ^{[1
]}

Soldi, Valdir ^{[2
]}

Merlo, Aloir Antonio ^{[3
]}

Montes D'Oca, Marcelo G. ^{[1
]}

机构：

[1] Univ Fed Rio Grande, Escola Quim & Alimentos, Lab Kolbe Sintese Organ, BR-96203000 Rio Grande, RS, Brazil

[2] Univ Fed Santa Catarina, Grp Estudo Mat Polimericos, BR-88040900 Florianopolis, SC, Brazil

[3] Univ Fed Rio Grande do Sul, Lab Sintese Organ & Mat Inteligentes, BR-91501970 Porto Alegre, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 19期

关键词：

Low-molecular-weight gelators; Fatty amino acids; L-Serine; Ricinoleic acid; L-ALANINE; DELIVERY; AMIDES; GELS;

D O I：

10.1016/j.tetlet.2012.03.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of L-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of L-serine in forming good gels. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2454 / 2460

页数：7

共 15 条

[1] First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills
Bhattacharya, S
Krishnan-Ghosh, Y
[J]. CHEMICAL COMMUNICATIONS, 2001, (02) : 185 - 186
[2] Physical gelation of binary mixtures of hydrocarbons mediated by n-lauroyl-L-alanine and characterization of their thermal and mechanical properties
Bhattacharya, Santanu
Pal, Asish
[J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (16) : 4918 - 4927
[3] Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation
Burstein, Sumner
Salmonsen, Rebecca
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (22) : 9644 - 9651
[4] Hoarau A. C. C., 2004, PHARM RES, V21, P454
[5] The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid L-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells
Lim, Li Yun Grace
Su, Yingying
Braet, Filip
Thordarson, Pall
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (07) : 653 - 656
[6] Self-assembled organogels formed by mono-chain L-alanine derivatives
Luo, XH
Liu, B
Liang, YQ
[J]. CHEMICAL COMMUNICATIONS, 2001, (17) : 1556 - 1557
[7] Synthesis and antituberculosis activity of new fatty acid amides
Montes D'Oca, Caroline Da Ros
Coelho, Tatiane
Marinho, Tamara Germani
Lopes Hack, Carolina Rosa
Duarte, Rodrigo da Costa
da Silva, Pedro Almeida
Montes D'Oca, Marcelo Goncalves
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) : 5255 - 5257
[8] Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids
Pal, Asish
Ghosh, Yamuna K.
Bhattacharya, Santanu
[J]. TETRAHEDRON, 2007, 63 (31) : 7334 - 7348
[9] First report on the efficacy of L-alanine-based in situ-forming implants for the long-term parenteral delivery of drugs
Plourde, F
Motulsky, A
Couffin-Hoarau, AC
Hoarau, D
Ong, H
Leroux, JC
[J]. JOURNAL OF CONTROLLED RELEASE, 2005, 108 (2-3) : 433 - 441
[10] RAGUNATHAN KG, 1995, CHEM PHYS LIPIDS, V77, P13

← 1 2 →